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$90+ Cheap flights from O'Hare Intl (ORD) to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Jun 19 — Jun 261
Thu 6/19
Thu 6/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Portland are usually found in August or September, booked 85 days in advance, depart on a Tuesday or Sunday and return on a Thursday

Cheap flight deals from O'Hare Intl to Portland

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 14, 2025.

Round-trip from

$236
(American Airlines)

One-way from

$90
(American Airlines)

Popular in

November

Cheapest in

August

Average price

$349

Good round-trip deal

$281 or less

Good one-way deal

$153 or less
From Chicago O'Hare Intl to Portland
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One-way flight from Chicago O'Hare Intl to Portland
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Highest demand for flights based on searches. 14% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Portland.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Portland.
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Find flight deals from O'Hare Intl to Portland

Cheapest flights from O'Hare Intl to Portland
Explore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 14, 2025.

This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/88:00 amORD - PWM
1 stop11h 24mAmerican Airlines
Tue 7/152:34 pmPWM - ORD
1 stop7h 57mAmerican Airlines
Deal found 6/12$236
This JetBlue deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/116:00 amORD - PWM
1 stop6h 23mJetBlue
Sat 8/162:20 pmPWM - ORD
1 stop9h 08mJetBlue
Deal found 6/13$237
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/14:46 pmORD - PWM
1 stop5h 28mUnited Airlines
Fri 7/45:35 amPWM - ORD
1 stop7h 08mUnited Airlines
Deal found 6/12$238
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/511:01 amORD - PWM
1 stop4h 10mDelta
Wed 8/136:00 amPWM - ORD
1 stop13h 02mDelta
Deal found 6/12$242
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/211:50 pmORD - PWM
1 stop5h 10mSouthwest
Sun 8/245:35 amPWM - ORD
1 stop7h 15mSouthwest
Deal found 6/13$279
This Sun Country Air deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/196:15 pmORD - PWM
1 stop16h 30mSun Country Air
Sat 7/2612:34 pmPWM - ORD
1 stop5h 53mSun Country Air
Deal found 6/12$295
This FlightHub deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/129:08 amORD - PWM
1 stop8h 05mFrontier
Sat 7/196:58 pmPWM - ORD
1 stop21h 45mFrontier
Deal found 6/12$327
This Trip.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/286:30 pmORD - PWM
Nonstop2h 31mMultiple Airlines
Mon 6/3012:16 pmPWM - ORD
1 stop5h 59mMultiple Airlines
Deal found 6/13$391

Cheapflights Fare Finder

Customize your flight search to find flights from O'Hare Intl to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 14, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland that are best for you.

Fly from

O'Hare Intl

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 7/8

8:00 am-8:24 pm

1 stop11h 24m

Portland

Tue 7/15

2:34 pm-9:31 pm

1 stop7h 57m

$236

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 8/11

6:00 am-1:23 pm

1 stop6h 23m

Portland

Sat 8/16

2:20 pm-10:28 pm

1 stop9h 08m

$237

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 7/1

4:46 pm-11:14 pm

1 stop5h 28m

Portland

Fri 7/4

5:35 am-11:43 am

1 stop7h 08m

$238

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 8/5

11:01 am-4:11 pm

1 stop4h 10m

Portland

Wed 8/13

6:00 am-6:02 pm

1 stop13h 02m

$242

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 8/21

1:50 pm-8:00 pm

1 stop5h 10m

Portland

Sun 8/24

5:35 am-11:50 am

1 stop7h 15m

$279

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 7/19

6:15 pm-11:45 am

1 stop16h 30m

Portland

Sat 7/26

12:34 pm-5:27 pm

1 stop5h 53m

$295

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 7/12

9:08 am-6:13 pm

1 stop8h 05m

Portland

Sat 7/19

6:58 pm-3:43 pm

1 stop21h 45m

$327

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 6/28

6:30 pm-10:01 pm

Nonstop2h 31m

Portland

Mon 6/30

12:16 pm-5:15 pm

1 stop5h 59m

$391

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 8/31

8:05 am-11:38 am

Nonstop2h 33m

$90

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 7/29

6:16 am-1:23 pm

1 stop6h 07m

$97

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

Showing 1-10 of 16 results
1
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Best time to book a flight from O'Hare Intl to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Portland

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Portland. Price data was last updated on June 9, 2025.

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Portland, Maine, you should look to book at least 85 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $296). Flying from Chicago O'Hare Intl Airport to Portland, Maine in July is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to PWM?

Find hourly flight availability from O'Hare Intl to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 14, 2025.

When flying from Chicago O'Hare Intl Airport to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 25% versus a flight in the morning.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Portland. Price data was last updated on June 8, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland, Maine flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Portland, Maine

Explore weekly flight availability from O'Hare Intl to Portland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 14, 2025.

The most flights from ORD to PWM are scheduled on a Monday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated June 14, 2025.
Read through reviews of airlines operating flights from Chicago to Portland, such as Southwest, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,283 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,283 reviews
Southwest
8.0
Very good
4,283 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,956 reviews
Southwest
8.0
Very good
4,283 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,793 reviews
Southwest
8.0
Very good
4,283 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,923 reviews
Southwest
8.0
Very good
4,283 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,283 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Chicago O'Hare Intl?

    For a flight from Chicago O'Hare Intl to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 7 inbound flights from Chicago O'Hare Intl per day. 4 airlines have flights to Portland from Chicago O'Hare Intl on a regular basis.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Portland, Maine round-trip?

    According to our current data, American Airlines ($236), JetBlue ($237), and United Airlines ($238) offers the cheapest pricing from Chicago O'Hare Intl Airport to Portland, Maine. You may be able to fly from Chicago O'Hare Intl Airport to Portland, Maine for 38% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Portland, Maine one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Portland, Maine are American Airlines ($90), JetBlue ($97), and Southwest ($100).

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Portland, Maine?

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Portland, Maine are American Airlines (100%), Envoy Air (100%) and Republic Airways (100%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Portland, Maine?

    While on average a flight from Chicago O'Hare Intl Airport to Portland, Maine is generally $467, our data shows the cheapest flight currently is $104. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $183 for that flight.

  • Can I find deals for flights from O'Hare Intl to Portland that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Portland.

  • Can I find deals for business class flights from O'Hare Intl to Portland?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $296). Flying from Chicago O'Hare Intl Airport to Portland, Maine in July is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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Top 4 airlines flying from O'Hare Intl to Portland

Discover the top 4 airlines that operate flights from O'Hare Intl to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$57Average$88FlexibilityNo cancel feeOn-time62%
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$176Average$331FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$213Average$385FlexibilityNo cancel feeOn-time69%

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